Diphenyl Ether → HCID 178487715, compound

HRID 964992Notes

Reaction equation

HRID 964992 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 178487721HCID 178487721, compound

Product 1

HCID 178487715HCID 178487715, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-7-methoxy-3-quinolinecarboxylic acid (21.4 g, 0.1 mol) was added with diphenyl ether (150 ml) and decarboxylated at 250° C. for 2 hours. The reaction mixture was allowed to cool to room temperature and added with ethyl acetate (300 ml). The resulting precipitates were collected by filtration to obtain crude 4-hydroxy-7-methoxyquinoline (15.0 g). This was recrystallized from water (about 300 ml) to obtain 14.8 g (86%) of 4-hydroxy-7-methoxyquinoline.

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. customto obtain crude 4-hydroxy-7-methoxyquinoline (15.0 g)
  4. customThis was recrystallized from water (about 300 ml)

Sources & evidence

ORD record
ord-f7deb334a8a449fd8a2480bcb32956cd
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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